EP4458906A1 - Vollaromatische etherketonharzzusammensetzung, formprodukt daraus und stabilisator auf phosphorbasis - Google Patents

Vollaromatische etherketonharzzusammensetzung, formprodukt daraus und stabilisator auf phosphorbasis Download PDF

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Publication number
EP4458906A1
EP4458906A1 EP22920683.4A EP22920683A EP4458906A1 EP 4458906 A1 EP4458906 A1 EP 4458906A1 EP 22920683 A EP22920683 A EP 22920683A EP 4458906 A1 EP4458906 A1 EP 4458906A1
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Prior art keywords
phosphate
metals
phosphates
ether ketone
dihydrogen
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EP22920683.4A
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English (en)
French (fr)
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EP4458906A4 (de
EP4458906B1 (de
Inventor
Ryo Takeuchi
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Polyplastics Co Ltd
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Polyplastics Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
    • C08G2650/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group
    • C08G2650/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group containing ketone groups, e.g. polyarylethylketones, PEEK or PEK
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • C08K2003/321—Phosphates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • C08K2003/321—Phosphates
    • C08K2003/324—Alkali metal phosphate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • C08K2003/321—Phosphates
    • C08K2003/325—Calcium, strontium or barium phosphate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • C08K2003/321—Phosphates
    • C08K2003/326—Magnesium phosphate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • C08K2003/329—Phosphorus containing acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/014—Stabilisers against oxidation, heat, light or ozone

Definitions

  • the present invention relates to a fully aromatic ether ketone resin composition, molded article thereof, and phosphorus stabilizer.
  • a fully aromatic ether ketone resin is also known as an abbreviation of polyaryl ether ketone (PAEK), and polyether ether ketone (PEEK), polyether ketone (PEK), polyether ketone ketone (PEKK), polyether ketone ether ketone ketone (PEKEKK), and the like are placed on the market as products. Since a fully aromatic ether ketone resin generally has a high melting point (over 300°C), it is necessary to heat the resin to a high temperature in melting the resin. However, at such a high temperature, there is a problem that stability to a thermal degradation is lacked. Therefore, various measures have been taken for stabilization in a molten state (see Patent Literatures 1 and 2). The stabilization to a thermal oxidation in a molten state is realized by adding a phosphate or a mixture of phosphates to resin compositions disclosed in Patent Literatures 1 and 2.
  • a fully aromatic ether ketone resin thickens in a molten state with increasing retention time. Such thickening is generally considered to be caused by crosslinking due to an oxidation in association with a processing temperature for a fully aromatic ether ketone resin being generally very high (over 350°C).
  • the resin compositions disclosed in Patent Literatures 1 and 2 are intended to achieve stabilization to the thermal oxidation in the molten state.
  • an increase or decrease in a viscosity with increasing retention time includes many factors such as a reaction between remaining reactive terminals, oxidative cross-linking, molecular chain elongation due to a side reaction by a remaining catalyst, and molecular chain breakage due to heat, oxygen, and residual impurities. Therefore, it is not possible to improve retention stability for melt viscosity simply by achieving stabilization to thermal oxidation.
  • a phosphate (a dihydrogen phosphate (NaH 2 PO 4 or the like) or a mixture of a dihydrogen phosphate and a hydrogen phosphate (Na 2 HPO 4 or the like)) has high metal corrosivity especially in the presence of water and at a high temperature. Therefore, when a phosphate is used for stabilization to a thermal oxidation in a molten state as described above, there is a possibility of corrosion of a metal members in equipment such as an extruder, and deterioration in manufacturability is of concern.
  • the present invention has been devised in view of the above problems in the past, and an object of the present invention is to provide a fully aromatic ether ketone resin composition having excellent retention stability of melt viscosity and manufacturability, a molded article thereof, and a phosphorus stabilizer excellent in metal corrosion resistance at a high temperature.
  • the present inventor found that the retention stability of the melt viscosity can be enhanced by adjusting the pH of the fully aromatic ether ketone resin composition to be in a predetermined range (neutral region). Further, the present inventor found that the metal corrosion resistance at a high temperature can be enhanced by using a specific phosphate in a specific combination, leading to the completion of the present invention.
  • One aspect of the present invention for solving the above problems is as follows.
  • the present invention it is possible to provide a fully aromatic ether ketone resin composition having excellent retention stability of the melt viscosity and excellent manufacturability, a molded article thereof, and a phosphorus stabilizer having low metal corrosivity at a high temperature.
  • Fig. 1 is diagram showing the relationship between pH and an ionic ratio of phosphates ([Na + ] / [P]) using a graph.
  • a fully aromatic ether ketone resin composition (hereinafter simply referred to as "resin composition") of the present embodiment contains (A) a fully aromatic ether ketone resin and (B) a phosphorus stabilizer. Further, (B) the phosphorus stabilizer contains (B1) a dihydrogen phosphate and (B2) a hydrogen phosphate. Still further, (B1) the dihydrogen phosphate is one or more dihydrogen phosphates of alkali metals, or one or more dihydrogen phosphates of metals selected from the group consisting of alkaline earth metals and magnesium.
  • the hydrogen phosphate is one or more hydrogen phosphates of alkali metals or one or more hydrogen phosphates of metals selected from the group consisting of alkaline earth metals and magnesium. If (B1) the dihydrogen phosphate is one or more dihydrogen phosphates of alkali metals, (B2) the hydrogen phosphate is one or more hydrogen phosphates of metals selected from the group consisting of alkaline earth metals and magnesium. If (B1) the dihydrogen phosphate is one or more dihydrogen phosphates of metals selected from the group consisting of alkaline earth metals and magnesium, (B2) the hydrogen phosphate is one or more hydrogen phosphates of alkali metals. The total amount of (B) the phosphorus stabilizer is 100 to 5000 mass ppm.
  • alkaline earth metals and the like metals selected from the group consisting of alkaline earth metals and magnesium are referred to as "alkaline earth metals and the like".
  • the pH of the fully aromatic ether ketone resin composition of the present embodiment is adjusted to be in a neutral region range by (B1) the dihydrogen phosphate and (B2) the hydrogen phosphate, and this can enhance the retention stability of the melt viscosity.
  • a mechanism thereof is inferred as follows.
  • the fully aromatic ether ketone resin to be polymerized by means of (1) the nucleophilic aromatic substitution reaction is polymerized under basic conditions at a high temperature (300°C or higher) using a phenolic hydroxyl group and an aromatic halogen as reactive groups.
  • a method for causing a terminal imbalance by means of a terminal blocking reaction and stopping the progress of polymerization is generally adopted ( Japanese Unexamined Patent Application Publication No. Sho 61-138626 ).
  • An alkali metal salt used as a basic catalyst is removed by washing with water after polymerization.
  • the dihydrogen phosphate is one or more dihydrogen phosphates of alkali metals or one or more dihydrogen phosphates of alkaline earth metals and the like.
  • the hydrogen phosphate is one or more hydrogen phosphates of alkali metals or one or more hydrogen phosphates of alkaline earth metals and the like.
  • a combination of (B1) the dihydrogen phosphate and (B2) the hydrogen phosphate has certain characteristics.
  • the hydrogen phosphate is a hydrogen phosphate of an alkaline earth metal and the like. Conversely, if (B1) the dihydrogen phosphate is one or more dihydrogen phosphates of alkaline earth metals and the like, (B2) the hydrogen phosphate is one or more hydrogen phosphates of alkali metals.
  • both of (B1) the dihydrogen phosphate and (B2) the hydrogen phosphate are alkali metal salts or salts of alkaline earth metals and the like, and if one of them is an alkali metal salt, the other of them is a salt of an alkaline earth metal and the like.
  • metal corrosion can be suppressed by combining (B1) the dihydrogen phosphate and (B2) the hydrogen phosphate as described above, and the mechanism thereof is inferred as follows. That is, an alkali metal phosphate is generally soluble in water, but the presence of a divalent or higher metal ion (in the present embodiment, an ion of an alkaline earth metal and the like) forms a salt indicated by M (I) M (II) PO 4 . Most of these salts are poorly soluble salts ( The journal of the Metal Finishing Society, Vol. 28, No. 1, 1977 ). Therefore, it is assumed that the solubility of a phosphate changed, the generation of an acid was suppressed, and the metal corrosivity decreased.
  • a fully aromatic resin composition of the present embodiment contains one or more selected from the group consisting of polyether ketone (PEK), polyether ether ketone (PEEK), and polyether ketone ether ketone ketone (PEKEKK), as (A) a fully aromatic ether ketone resin.
  • PEK polyether ketone
  • PEEK polyether ether ketone
  • PEKEKK polyether ketone ether ketone ketone ketone
  • A a fully aromatic ether ketone resin.
  • Fully aromatic ether ketone resins are basic because the resins are polymerized by means of (1) the nucleophilic aromatic substitution reaction. From this viewpoint, the pH of the fully aromatic ether ketone resin itself is preferably 9 to 12.
  • the fully aromatic ether ketone resin is preferably polyether ketone (PEK).
  • polyether ketone ketone As described above, there are two methods for polymerizing the fully aromatic ether ketone resin: (1) the nucleophilic aromatic substitution reaction and (2) the Friedel-Crafts acylation reaction.
  • PEKK polyether ketone ketone
  • Such polyether ketone ketone (PEKK) exhibits neutrality.
  • the phosphorus stabilizer contains (B1) the dihydrogen phosphate and (B2) the hydrogen phosphate.
  • B1) The dihydrogen phosphate and (B2) the hydrogen phosphate will be described below individually.
  • the dihydrogen phosphate used in the present embodiment is one or more dihydrogen phosphates of alkali metals or one or more dihydrogen phosphate of alkaline earth metals and the like.
  • dihydrogen phosphates of alkali metals examples include potassium dihydrogen phosphates, sodium dihydrogen phosphates, lithium dihydrogen phosphates, rubidium dihydrogen phosphates, cesium dihydrogen phosphates, and the like.
  • dihydrogen phosphates of alkaline earth metals and the like includes magnesium dihydrogen phosphates, calcium dihydrogen phosphates, strontium dihydrogen phosphates, barium dihydrogen phosphates, and the like.
  • the dihydrogen phosphate is preferably a dihydrogen phosphate of one or more metals selected from the group consisting of sodium, potassium, magnesium, and calcium.
  • the hydrogen phosphate used in the present embodiment is one or more hydrogen phosphates of alkali metals or one or more hydrogen phosphates of alkaline earth metals and the like.
  • Examples of hydrogen phosphates of alkali metals include dipotassium hydrogen phosphates, disodium hydrogen phosphates, dilithium hydrogen phosphates, dirubidium hydrogen phosphates, dicesium hydrogen phosphates, and the like.
  • Examples of hydrogen phosphates of alkaline earth metals and the like include magnesium hydrogen phosphates, calcium hydrogen phosphates, barium hydrogen phosphates, and the like.
  • the hydrogen phosphate is preferably a hydrogen phosphate of one or more metals selected from the group consisting of sodium, potassium, magnesium, and calcium.
  • examples of combinations of (B1) the dihydrogen phosphate and (B2) the hydrogen phosphate include the following, but the combinations are not limited to the following in the present embodiment.
  • Fig. 1 is a graph showing the relationship between the pH and an ionic ratio of phosphates ([Na + ] / [P]).
  • a composition when a value of [Na + ] / [P] is 1.00, a composition is NaH 2 PO 4 , and when a value is 2.00, a composition is Na 2 HPO 4 .
  • a value of [Na + ] / [P] is more than 1.00 and is less than 2.00, a composition is a mixture of NaH 2 PO 4 and Na 2 HPO 4 . In this state, the pH is in the neutral region, and the retention stability of the melt viscosity is enhanced.
  • the total amount of (B) the phosphorus stabilizer described above is 100 to 5000 mass ppm. If the amount is less than 100 mass ppm, the retention stability of the melt viscosity is inferior, and if the amount is more than 5000 mass ppm, the manufacturability is inferior.
  • the amount is preferably 100 to 1000 mass ppm, and more preferably 200 to 800 mass ppm.
  • thermoplastic resin in the present embodiment, one or more of the following can be added to a thermoplastic resin as common additives when needed: a lubricant, a mold release agent, an antistatic agent, a surfactant, a flame retardant, an organic polymer material, and an inorganic or organic powdery state or platelike filler.
  • a lubricant e.g., a lubricant, a mold release agent, an antistatic agent, a surfactant, a flame retardant, an organic polymer material, and an inorganic or organic powdery state or platelike filler.
  • the resin composition of the present embodiment does not contain moisture in order to further enhance metal corrosion resistance.
  • a molded article of the present embodiment is obtained by molding the fully aromatic ether ketone resin composition of the present embodiment described above. Since the resin composition has excellent retention stability of the melt viscosity, the molded article can be stably used even if the molded article is obtained by performing a molding processes involving a long-time exposure to a high temperature, such as continuous molding for a long time by injection molding or solid phase extrusion with a long retention time. Further, since the resin composition has excellent manufacturability, corrosion in a manufacturing apparatus is reduced during molding of the molded article.
  • the fully aromatic ether ketone resin composition of the present embodiment is put into an extruder, and then melt-kneaded and pelletized to form a pellet, then the pellet is put into an injection molding machine having a predetermined mold, and accordingly the molded article can be fabricated by means of injection molding, for example.
  • the molded article of the present embodiment can be suitably used for use applications such as automobiles, aviation, heavy industry (steel and power plants), and electronic components.
  • the phosphorus stabilizer of the present embodiment contains (B1) the dihydrogen phosphate and (B2) the hydrogen phosphate.
  • the dihydrogen phosphate is one or more dihydrogen phosphates of alkali metals or one or more dihydrogen phosphates of metals selected from the group consisting of alkaline earth metals and magnesium.
  • the hydrogen phosphate is one or more hydrogen phosphates of alkali metals or one or more hydrogen phosphates of metals selected from the group consisting of alkaline earth metals and magnesium.
  • the hydrogen phosphate is one or more hydrogen phosphates of metals selected from the group consisting of alkaline earth metals and magnesium. If (B1) the dihydrogen phosphate is one or more dihydrogen phosphates of metals selected from the group consisting of alkaline earth metals and magnesium, then (B2) the hydrogen phosphate is one or more hydrogen phosphates of alkali metals.
  • the phosphorus stabilizer of the present embodiment is (B) the phosphorus stabilizer contained in the fully aromatic ether ketone resin composition of the present embodiment described above. Therefore, when the stabilizer is added to the fully aromatic ether ketone resin composition, the retention stability of the melt viscosity is excellent. In addition, since the phosphorus stabilizer of the present embodiment has low metal corrosivity at a high temperature, when the stabilizer is added to the fully aromatic ether ketone resin composition and then extruded by an extruder, it is possible to prevent corrosion of a metal member inside the extruder, for example.
  • the phosphorus stabilizer of the present embodiment is (B) the phosphorus stabilizer contained in the fully aromatic ether ketone resin composition of the present embodiment described above, and the description already made for (B) the phosphorus stabilizer applies without any changes.
  • the preferred aspects and specific examples in the description made for (B) the phosphorus stabilizer are also the same. Therefore, a detailed description of the phosphorus stabilizer of the present embodiment will be omitted.
  • the phosphorus stabilizer of the present embodiment does not contain moisture for further enhancement of metal corrosion resistance.
  • phosphorus stabilizers were obtained by blending (B1) the dihydrogen phosphate and (B2) the hydrogen phosphate shown in Tables 1 and 2 in the ratios shown in Tables 1 and 2. Further, assuming that the number of moles of alkali metals is [M I ], the number of moles of alkaline earth metals and the like is [M II ], and the number of moles of phosphorus is [P], Tables 1 and 2 show calculated numerical values using a formula ([M I ] + [M II ] * 2) / [P] .
  • the metal corrosion resistance of a phosphorus stabilizer obtained in each example, comparative example, and reference example was evaluated by performing an accelerated test according to the following procedure.
  • Example 1 Example 2
  • Example 3 Example 4
  • Example 5 Example 6
  • Example 7 Phosphorus stabilizer (B1) Dihydrogen phosphate Sodium dihydrogen phosphate g 4.0 - - - - - 7.5 Potassium dihydrogen phosphate g - 7.5 - - - 8.0 - Magnesium dihydrogen phosphate g - - - - 9.7 - - Calcium dihydrogen phosphate g - - 11.5 12.8 - - - Ammonium dihydrogen phosphate g - - - - - - - (B2) Hydrogen phosphate Disodium hydrogen phosphate g - - 3.5 - 5.3 - - Dipotassium hydrogen phosphate g - - -
  • Tables 1 and 2 reveal that, in the evaluation of the metal corrosion resistance, good results were obtained in all Examples 1 to 7, while poor results were obtained in all Comparative Examples 1 to 7.
  • the metal corrosion resistance at a high temperature is enhanced by using (B1) the dihydrogen phosphate and (B2) the hydrogen phosphate in a predetermined combination, while containing a predetermined amount of a phosphorus stabilizer as a whole.
  • Reference Example 1 is an example in which a disodium hydrogen phosphate is added alone as (B2) the hydrogen phosphate. When a hydrogen phosphate is used alone, a problem of inferior metal corrosion resistance does not occur.
  • Polyether ketone powder was obtained by performing polymerization according to a manufacturing method disclosed in JP 2009-227961 A .
  • the powder of the fully aromatic ether ketone resin composition obtained in each example and comparative example was melt-kneaded at a barrel set temperature of 380°C, and a die head set temperature of 400°C, using a twin screw extruder ZSK26MC manufactured by Coperion GmbH to obtain a resin composition pellet.
  • the melt viscosity of the obtained resin composition pellet was measured at a cylinder temperature set value of 400°C and a shear rate of 1000/second in accordance with ISO11443 using an orifice with an inner diameter of 1 mm and a length of 30 mm and using a CAPILOGRAPH 1B manufactured by Toyo Seiki Seisaku-sho, Ltd.
  • Evaluation was made based on the retention of the melt viscosity calculated in each example and comparative example. That is, if the retention of the melt viscosity was 95% or more and less than 105%, it was evaluated as "good”, and if the retention was less than 95%, or was 105% or more, it was evaluated as "poor”. When an evaluation result was "good", this indicates that the retention stability of the melt viscosity is excellent. Tables 3 and 4 show evaluation results.
  • the manufacturability of resin compositions of each example and comparative example was determined based on test results of the metal corrosion resistance of phosphorus stabilizers in Examples 1 to 6, Comparative Examples 1 to 7, and Reference Example 1 descried above. That is, the manufacturability was determined based on test results of the metal corrosion resistance of phosphorus stabilizers in Examples 1 to 6, Comparative Examples 1 to 7, and Reference Example 1 corresponding to (B) the phosphorus stabilizers used in each example and comparative example. Specifically, if the weight loss was 4% or less, the example was evaluated as "good", and if the weight loss was more than 4%, it was evaluated as "poor".
  • Example 8 Example 9
  • Example 10 Example 11
  • Example 12 Example 13 (A) Fully aromatic ether ketone resin Polyether ketone g 3000 3000 3000 3000 3000 3000 3000 (B) Phosphorus stabilizer (B1) Dihydrogen phosphate Sodium dihydrogen phosphate ppm 70 - - - - - Potassium dihydrogen phosphate ppm - 200 - - - 340 Magnesium dihydrogen phosphate ppm - - - - 310 - Calcium dihydrogen phosphate ppm - - 560 950 - - Ammonium dihydrogen phosphate ppm - - - - - - - (B2) Hydrogen phosphate Disodium hydrogen phosphate ppm - - 170 - 170 - Dipotassium hydrogen
  • Tables 3 and 4 reveal that, in Examples 8 to 13, the retention stability of the melt viscosity and the manufacturability of resin compositions are excellent. Meanwhile, in Comparative Examples 8 to 17, it is not possible to satisfy both the retention stability of the melt viscosity and the manufacturability of the resin compositions simultaneously.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP22920683.4A 2022-01-11 2022-12-28 Vollaromatische etherketonharzzusammensetzung, formkörper daraus und phosphorhaltige stabilisatoren Active EP4458906B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2022002415 2022-01-11
PCT/JP2022/048558 WO2023136168A1 (ja) 2022-01-11 2022-12-28 全芳香族エーテルケトン樹脂組成物及びその成形品、並びにリン系安定剤

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EP4458906A1 true EP4458906A1 (de) 2024-11-06
EP4458906A4 EP4458906A4 (de) 2025-04-09
EP4458906B1 EP4458906B1 (de) 2026-04-01

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US (1) US20250092221A1 (de)
EP (1) EP4458906B1 (de)
JP (1) JP7332840B1 (de)
CN (1) CN118510848A (de)
TW (1) TW202336154A (de)
WO (1) WO2023136168A1 (de)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0184458B1 (de) 1984-12-05 1989-10-18 Imperial Chemical Industries Plc Thermoplastische aromatische Polyetherketone
CN1234774C (zh) 2000-06-02 2006-01-04 汎塑料株式会社 阻燃树脂组合物
EP2105430B1 (de) 2008-03-24 2011-11-16 Gharda Chemicals Limited Polyetherketon, sein Monomer und Phenolat
CN101892602B (zh) * 2010-07-19 2012-01-11 上海长胜纺织制品有限公司 冷转移印花糊料、其印花色浆及其制备方法
FR3039157B1 (fr) 2015-07-22 2019-06-28 Arkema France Composition a base de polyarylene-ether-cetone (paek) stable a l'etat fondu et procede de stabilisation d'une telle composition
JP6694657B2 (ja) * 2015-12-22 2020-05-20 株式会社カネカ ポリオルガノシロキサン粒子含有グラフト共重合体およびその熱可塑性樹脂組成物
JP6938539B2 (ja) * 2016-04-29 2021-09-22 ソルベイ スペシャルティ ポリマーズ ユーエスエー， エルエルシー 相溶化ポリマー組成物
WO2019243270A1 (en) * 2018-06-21 2019-12-26 Solvay Specialty Polymers Usa, Llc Poly(ether ketone ketone) (pekk) composites
FR3093666B1 (fr) * 2019-03-15 2022-01-14 Arkema France Procédé de fabrication par frittage d'une poudre à base de poly-aryl-éther-cétone(s) en partie recyclée

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JPWO2023136168A1 (de) 2023-07-20
CN118510848A (zh) 2024-08-16
WO2023136168A1 (ja) 2023-07-20
EP4458906A4 (de) 2025-04-09
US20250092221A1 (en) 2025-03-20
EP4458906B1 (de) 2026-04-01
JP7332840B1 (ja) 2023-08-23

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